The Parisian flâneur is a figure whose indulgent urban loitering is shaped by straight white male privilege. In contrast, this essay introduces the concept of the Blackqueer flâneuse, highlighting the radical imagination’s role in maneuvering through heavily surveilled and controlled spaces. By weaving together intersecting theories of waywardness (Hartman) and willfulness (Ahmed), it examines Black flâneuserie —both as an imaginative and tangible mode of mobility— that ingeniously subverts or sidesteps the violence of capture. Focusing on Laila Green, from the series In Treatment (2021), the essay unveils her outlaw imagination, her yearning for liberation, and her everyday practices of wandering as alternative expressions of flâneuserie. Employing the concept of queer failure (Halberstam), the analysis frames Laila’s persistent attempts at escape alongside her history of facing setbacks as a practice of flâneuserie. With the help of critical geography (de Certeau, Tuan, Cosgrove, Cosgrove and Dora) and Jungian theory, it conceptualizes Laila’s passion for high places and mountains and ultimately the realization of her passion as evidence of her individuation. Akin to the paradoxes of white male flânerie, Black flâneuserie in Laila’s case unfolds as a paradoxical journey of self-discovery, complicated by her privilege and the entanglements of her wanderings within the logic of racial capitalism.